


The One Where the Stripper Cries

by internationalfandomgirl



Category: Supernatural
Genre: Gen, Stripper!Reader, Strippers, awkward lap dances because of the situation, hunter!sister
Language: English
Status: Completed
Published: 2018-01-02
Updated: 2018-01-02
Packaged: 2019-02-27 10:48:31
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,358
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13246629
Author URL: https://archiveofourown.org/users/internationalfandomgirl/pseuds/internationalfandomgirl
Summary: Y/N Winchester is the oldest child of John and Mary Winchester. You left the family at 18. You got out of the busniess, mostly, only going on hunts near by. A hunt requires you to go undercover as a stripper. Little do you know that your brothers also are on the hunt.





	The One Where the Stripper Cries

**Author's Note:**

> This is my enry for @imjusthereforsupernatural The One With Jo’s Celebration Challenge. Congrats on 1,500 followers! I’m sorry I am so late on this, I’ve been really struggling with my inspiration lately.

The Winchester siblings are well known in the hunting community, especially the brothers. Most people don’t know about the oldest Winchester, Y/N. You are a great hunter, but you got out as soon as you turned 18. Little Sammy tried to follow in your footsteps until Dean came and dragged him back into the life. Dean wanted to find you as well but you had gone radio silent on him about a year before your dad’s disappearance. You would stick to cases near where you call home. Today you found yourself in a small town not too far from home. At a strip bar of all places. You were going to have to go undercover to figure this thing out and you were not looking forward to it. You a stripper.

“Ugh, here we go,” you sigh pulling your coat around you tight before heading into the club to get to work.

—

The Winchester brothers pulled up to a club. “Is this why you wanted to do this hunt so badly? It involves a strip club?” Sam scoffed at his brother who was smiling like a five-year-old.

“If you can’t beat ‘em join ‘em Sammy!” Dean laughed as he shut the door to the impala and made his way into the club.

The boys found their way to a table in the corner and order themselves a drink while they observed the people around them.

“He Sweetpea, two guys came in about 20 minutes ago and they’ve only been drinking. Why don’t you head on over and see if you can entice them to spend a little more?” You nod your head that you heard your boss before heading off to the men in the corner.

“Hey Dean, doesn’t that girl look familiar to you,” Sam asked pointing towards you.

“Yea, maybe,” Dean says before taking a drink of his beer. You step up to the table as he spits it right back out. “Holy shit! Y/N?!”

“Shhhhh! Fuck what are you two doing here? You are going to blow my cover.”

“Your cover,” Sam asks.

“You are a stripper,” Dean exclaims.

“Shut up Dean! Seriously, the boss sent me over here to convince you guys to spend money on more than just beer. Also, don’t call me Y/N. It’s Sweetpea. Now in order for us to keep talking I’m gonna have to dance for one of you. Otherwise we are going to have to wait until the shift is over and talk somewhere else.” Dean threw some money on the table. “God this is going to be awkward,” you mumbled as you started dancing.

“So you are undercover, what do we know so far,” Dean asks.

“As awkward as this is going to be for all of us Dean, you need to act as if I’m actually a stripper and you are enjoying this or else this little reunion we have going here is going to get broken up by the boss man.” You look at Dean pleading with your eyes before you look over your shoulder to see your boss watching you. Turning back, you start dancing again. “Okay, so we are dealing with a demon and the demon is someone connected to this club. I figure it is someone who works here, I’m just trying to figure out it is now.”

“Do you have any ideas of who it might be Sweetpea?” Sam asks while trying to look interested in what is happening around the club as the song ended.

“Dang it. You have to put out some more money or I have to move on.” Dean threw down more money on the table and nodded over towards Sam. You stood up and moved over to Sam and started dancing again. “I thought it would be the boss man because he gives me all sorts of creeps, but I have been putting holy water into his drink every time I have to deliver one to him.”

“So no other leads then,” Sam asks looking nowhere but your face.

“Not yet. My break is up after this song. I plan to go backstage and talk to the girls before the big numbers start,” you smile shyly at your youngest brother.

“Well, umm, what do you want us to do,” he asks.

“We keep an eye on the other girls, obviously Sam.” Dean says as if it is the most obvious answer in the world.

You roll your eyes as you stand up from Sam grabbing the money off the table and heading towards the backstage room.

You were walking through the room full of girls preparing for their big numbers you were whispering ‘Christo’ trying to find the girl who was being possessed by a demon. All of a sudden you were being called to stage. As you walked past Cherry you said one last ‘Christo’ and watched her react. You had found the demon right as you were shoved on the stage to dance. As you started to move you saw Cherry walk out onto the floor. You made eye contact with you brothers and then peered at her. Willing them to understand what you were trying to tell them. You saw Sam nod and stand up following the women.

When you came off the stage you heard yelling in one of the private rooms. You ran there as fast as you could the door was locked, so you slammed into it with your shoulder, breaking the hinge. Inside were your brothers and the demon. Come to find out the demon was screaming because Dean was saying an exorcism. Sam was struggling to hold her so you helped hold her until it was finished.

After the last words were said she crumbled into you. Sam let go and let you slowly take her to the floor into your arms as the girl came to. She looked into your face and started crying. “Shhhhh sweetheart, you are okay. Everything is okay. You are going to be okay.”

She looked up at you, “I killed them.”

“It wasn’t you, you had no control over it. You are going to be okay.” She continued to cry into you as you comforted her.

You were finally able to leave the strip club after your shift ended. You walked out of the building to see the car you never thought you were going to see again in your life. “So Dean do all of your nights at the strip club end with the stripper crying or was tonight just special?”

“Ha!” Sam laughs at Dean’s reaction. He raises his hand for a high five which you give. Dean gives the two of you a bitch face.

“Oh come on Dean-o! You know that was funny. I’m sure you give little Sammy the same type of crap.”

Dean rolled his eyes towards you while mumbling, “stupid older sisters anyways.”

“Excuse me,” you raise an eyebrow at him, “what did you say?”

“Nothing,” he looks down at the ground.

“That’s what I thought Dean-O,” you smile at him.

“It’s Dean.”

“I know Dean. I’m just giving you shit. Like you do to Sam,” you nod towards your youngest brother. “I know you like calling him Sammy, Samantha, Samuel. All the things he doesn’t like to be called. Hey, I’m the oldest, it is my job to make your life miserable, remember?”

“Hey, Y/N. Why don’t you come with us,” Sam half asks and half pleas with you.

“I wish I could Sam, but this is my home now. I need to stay here. We can keep in touch though, okay?” You give him a hug and then hand him a paper with your number on it.

“You two be careful you hear?”

Dean gives you a hug, “always sis. Seriously though, keep in touch.”

“Communication is a two-way street there,” you smile back at him as he climbs into the car. You smile and wave at your brothers as Dean starts up the car and pulls away. You couldn’t help but keep that smile on your face. Your brothers have certainly grown up into some great young men.


End file.
